Most Stylish Moments of 2008

The premiere of The Pineapple Express

For reasons we still can't quite comprehend (though that may be the after-effects of the after-party at Seth Rogen's pad), the red carpet for a stoner comedy somehow turned into a catwalk. James Franco sported a spiffed-up shawl-collared suit, Kanye West rocked YSL, and Daniel Craig showed up in a Tom Ford three-piece. Whatever those guys were smoking, we want some.Photo: Frazer Harrison/Getty Images

Sam Riley in Burberry's fall campaign

Christopher Bailey couldn't resurrect Ian Curtis for Burberry's Mario Testino–shot fall campaign, so he did the next best thing: He hired the guy who played him. (The Joy Division singer's influence shouldn't be underestimated.)Photo: Burberry

Mark Ronson tours with Jay-Z

At a series of U.K. shows this summer, Jay-Z reminded us why he's the world's top MC. The leader of his backing band, meanwhile, reminded us why he's the world's best-dressed DJ-producer. Who knew that Gram Parsons–meets–junior prom could look this sharp?Photo: Shirlaine Forrest/WireImage.com

Freddy Rumsen's send-off on Mad Men

If your idea of a productive morning at work involves pissing your pants, blacking out, and blowing off a big pitch meeting, let's hope you've got bosses like Don Draper and Roger Sterling. No, Rumsen couldn't be allowed to keep pulling that kind of shit—not even in 1962—but it's just not classy to cut a lifer like Freddy loose without first logging a few boozy hours at a shady after-hours joint. (Got that, boss?)Photo: Courtesy of AMC

Daniel Day-Lewis at the Oscars

The merits of DDL's scenery-chewing in There Will Be Blood inspired more than a little debate (in our offices, at least), but the former cobbler's brown suede shoes—which smartly matched the piping on his Paul Smith tux—was the consensus pick for the red-carpet's standout performance (in our offices, at least).Photo: Dan MacMedan/WireImage

Karl Lagerfeld makes a PSA for French traffic safety

He may be the Kaiser, but evidently Karl Lagerfeld isn't above putting on a brightly colored vest (over Dior Homme, naturally) in the cause of encouraging drivers to do the same during nighttime roadside incidents. We look forward to Calvin Klein's "Give 'Em a Brake" campaign in 2009.Photo: vogue.co.uk

Adam Kimmel Claremont HD

While Lagerfeld was promoting traffic safety in France, Adam Kimmel was undermining it in California. This video, which features the Kimmel-besuited Noah Sakamoto and Patrick Rizzo whizzing down a seemingly endless hilltop two-lane road outside L.A., is nothing if not harrowing. After all, one false move and the skate legends could be total goners. Even worse, they'd ruin such nice clothes.Photo: Adam Kimmel

Taz from Sa-Ra, a model from Ann Demeulemeester's show, and Kanye West

Not just one of the year's most stylish moments, but also one of the most fortuitous. After all, how often would Kanye (right, in Pastelle), Taz (left, in MCM and, uh, leggings), and this old guy cross paths? The fact that Scott Schuman was on hand to snap it makes it all the more memorable. (It's also a reminder that style and wearability don't always have to be synonymous.)Photo: Scott Schuman

The all-too-short heyday of Muxtape

There are plenty of music sites on the Web, but none has Muxtape's sense of style—or combination of cutting-edge streaming technology with retro presentation. Not even Muxtape, it turns out. The killjoys at the RIAA shut the virtual-mix-tape site down in August, five months after it went live. We'll call that one of the year's least stylish moments.Photo: Muxtape

Robert Redford and Bono at Sundance

The Sundance Kid has long been a poster boy for aging with grace. Squint a bit and you might think he'd just stepped off the set of Three Days of the Condor. (His comrade, regrettably, looks like he just stepped out of Moscow on the Hudson.)Photo: Fred Hayes/WireImage

Mickey Rourke at the Venice International Film Festival

In 2008, it seemed like ol' Mickey couldn't hit a wrong note—either that, or he hit so many wrong ones everything somehow went right. That's true both for his acting in The Wrestler and his red-carpet attire. Where else did a fat tie, popped collar, greasy hair, cigar, and geriatric Chihuahua look this snazzy?Photo: Daniele Venturelli/WireImage

Daniel Craig pays homage in Quantum of Solace

Steve McQueen ain't exactly the most innovative fashion inspiration in this day and age, but the subtle Great Escape homage seen here—the jacket's Y-3, by the way—is hard to fault. In fact, it kind of reminds us how McQueen got to be so damn influential in the first place.Photo: Columbia Pictures

Tom Ford takes matters into his own hands

Like a certain Paris-based fashion legend (hint: he's deeply concerned about roadside safety), this year Tom proved he's as adept with a camera as he is with a sketchbook. Here's the story: Evidently displeased with the stiff poses in his original Spring '09 lookbook, the designer decided to reshoot the damn thing himself. Perhaps not the kind of hands-on approach recommended in your typical management handbook, but it's hard to argue with the results. (Note: This doesn't necessarily mean that Tom personally did the pick-stitching on your new suit.)Photo: Tom Ford

Rafael Nadal at the U.S. Open

Back in August, Nike announced with great fanfare that Rafael Nadal would be trading in his signature clam-digger-on-steroids look for more a traditional tennis-shorts-and-polo ensemble (with sleeves, even). Evidently, Rafa never got the memo, because when the Open kicked off, there he was in a tight-fitting tank and capri pants. While we're stopping short of actually endorsing the look, we respect the guy for sticking to his, ahem, guns.Photo: Elsa/Getty Images

The "r" in the Rogan Bouwerie sign

The oppressive, all-black interior of Rogan's new shop probably seemed like a better idea on paper than it turned out to be in practice, but giving a subtle typographical tweak to the 1974-vintage sign was downright inspired—not unlike the designer's sartorial tweaks to American classics.Photo: Racked

Stefano Pilati at Yves Saint Laurent's funeral

Here's a sartorial conundrum for you: When one of the all-time legends of fashion dies—and you just happen to be the designer of his namesake label—what do you wear to the funeral? (Oh, and did we mention this is happening in France?) That sort of thing would break a lesser man, but not Stefano Pilati, who remained cool, stuck to his signature mix of refinement and panache, and reminded us why he's one of the best-dressed men in menswear.Photo: Marc Susset-Lacroix/WireImage

Leonardo DiCaprio in Revolutionary Road

Thank costume designer Albert Wolsky for Leo DiCaprio's smart, pre–Mad Men getups in Revolutionary Road—but thank the actor himself for this effortlessly elegant moment between takes. Is it just us, or are pleated pants suddenly due for a serious comeback?Photo: James Devaney/WireImage

David Beckham at the ESPYs

Most athletes plan their ESPYs outfits with all the forethought the irrelevant little affair deserves. Which is to say: a squirt of Dep gel and, if you're feeling ambitious, that maroon eight-button suit you wore on draft day. Not Becks, though, who turned up at this year's event in an impeccably tailored tux. Does the guy care a bit too much about fashion over sport? Perhaps, but then, have you ever seen Steve Nash dress this well?Photo: Stephen Shugerman/Getty Images

Barack Obama rips off a few pull-ups in Missoula, Montana

Photographer Callie Shell tells it best: "Two staffers had just passed this site and done two pull-ups. Not to be outdone, Obama did three with ease, dropped, and walked out to make a speech." Sure, the man's ties are elegant and the suits fit relatively well, but sometimes style is less about the clothes you're wearing than what you do while wearing them.Photo: Callie Shell

Charlie Rose plays hurt

Falling down and taking one in the face to save your spiffy new MacBook Air? A little stupid, if you ask us. Going on the air afterward anyway, shiner be damned? Now that's style. And besides, black eyes go great with Purple Label.Photo: PBS

Terry cleans up nice

Hey, when your beloved plaid flannel has been co-opted by workwear-fixated fashion designers and your photographic style is being ripped off by wannabes left and right, sometimes putting on a suit and heading off to the American Museum of Natural History Winter Dance is the most subversive thing a guy can do.Photo: Will Ragozzino/Getty Images

Wellingtons at Reading

Sure, seeing a bunch of Brits in wellies is about as newsworthy as an Illinois governor arrested for corruption, but even so, at this year's muddy fest, the fellers managed to outshine the birds.Photo: Alistair Guy

Dave and Conan's strike beards

Dave's solidarity-inspired facial growth served only to complement his newfound avuncular persona. But the new neck scruff really seemed to bring out the best in his fellow desk jockey. To put it another way, we don't think it's a coincidence that a hirsute Conan was looser, weirder, and yes, funnier than he had been in years.Photo: NBC/CBS

Scott Campbell does Mother's Day

However you feel about Mother's Day tattoos—or tattoos in general—you've got to hand it to Scott Campbell. In honor of his own dearly departed mom, the legendary ink-slinger spent Mother's Day 2008 at Earnest Sewn giving people tats for 100 bucks a pop. (Watch our video of the event here.)Photo: Staff

Dominic Cooper in Milan

Consider this photo Exhibit A in one of menswear's most elemental equations. To wit: Take a handsome young actor (British, if possible), add a nicely tailored suit, plus an Italian café as backdrop, plus some guy named The Sartorialist, and you've got the makings of one sharp-looking pic. See? Looking good is easy.Photo: Scott Schuman